Oakland Vacations from $241
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was $323, price is now $241 per person
$241
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8/10 Very Good! (1,003 reviews)
Very friendly staff. Extremely clean and large room.
Reviewed on Dec 13, 2025
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $357, price is now $247 per person
$247
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
clean and comfortable!
Reviewed on Dec 8, 2025
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $576, price is now $404 per person
$404
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,003 reviews)
Nice hotel in downtown Pittsburgh. Room and common area were clean and well maintained.
Reviewed on Dec 8, 2025
Kimpton Hotel Monaco Pittsburgh by IHG
Downtown Pittsburgh
Price was $466, price is now $348 per person
$348
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,253 reviews)
Room was immaculately cleaned. Staff was friendly and helpful.
Reviewed on Dec 9, 2025
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $423, price is now $318 per person
$318
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Everyone I encountered was amazing through our experience related to our stay. There was an event occurring in the main entry way during our stay and the valet assisted us in locating parking, called the front desk and checked in from the door, they were very informative and helpful, even the building staff were very friendly and helpful helped us with the door on arrival. It would be nice to be able to use valet service, especially since it is paid parking anyways, and also enter through the nicer main lobby rather than a service entrance and padded frieght elevator... I did chose the Penn because of its prestige, location, amenities, and to view/enjoy craftsmanship of the architecture and chandilers specifically (as a former apprentice of the artist). Overall great stay.
Reviewed on Dec 9, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Dec 21 to Dec 22
$139 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (540 reviews)
Friendly staff, beautiful clean rooms
Reviewed on Dec 8, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$110 nightly
The price is $125 total per night from Dec 25 to Dec 26
$125 total
Dec 25 - Dec 26
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Staff, Clean room. TV and lobby computersuch disappointment.
Reviewed on Dec 4, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $214 total per night from Dec 21 to Dec 22
$214 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (719 reviews)
Beautiful hotel with great staffs and convenient location.
Reviewed on Dec 4, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
4.5/5(48 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
5/5(4 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$102
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
$235
per adult
Explore a world of travel with Expedia
- Pittsburgh Hotels
- Hotels near Downtown Pittsburgh
- Hotels near University of Pittsburgh
- Hotels near University of Pittsburgh Medical Center
- Hotels near Petersen Events Center
- Hotels near Soldiers and Sailors Memorial Hall and Museum
- Hotels near Cathedral of Learning
- Hotels near Heinz Memorial Chapel
- Hotels near Carnegie Library of Pittsburgh
- Hotels near North Oakland
- Hotels near Carnegie Museum of Natural History
- Hotels near Pittsburgh Playhouse
- Hotels near Central Oakland
- Hotels near Tour-Ed Mine
- Hotels near Carnegie Museum of Art
- Cheap Hotels in Pittsburgh
- Hotels near PNC Park
- Hotels near Phipps Conservatory
- Hotels near PPG Paints Arena
- Hotels near Carnegie Mellon University
- Hotels near South Oakland
- Hotels near Schenley Park
- Hotels near Acrisure Stadium
- Hotels near UPMC Shadyside
- Hotels with Free Airport Shuttle in Pittsburgh
- Hotels near Shadyside
- Hotels near Strip District
- Hotels near Pittsburgh Opera
- Hotels near Gallery G Glass
- Extended Stay America Hotels in Shadyside
- Boutique Hotels in Shadyside
- Extended Stay Hotels in Shadyside
- Marriott Hotels & Resorts in Shadyside
- Luxury Hotels in Shadyside
- Hotel Wedding Venues Hotels in Shadyside
- Resorts & Hotels with Spas in Shadyside
- Hotels with Free Parking in Shadyside
- Hotels with a Swim-up Bar in Shadyside
- 4 Star Hotels in Shadyside
- Hotels with Laundry Facilities in Shadyside
- Cheap Hotels in Shadyside
- 5 Star Hotels in Shadyside
- Hotels with Hot Tubs in Shadyside
- Hotels with Bars in Shadyside
- Romantic Hotels in Shadyside
- Hotels with Fireplaces in Shadyside
- Casino Hotels in Shadyside
- Hotels near Bloomfield
- 4 Star Hotels in Bloomfield
- Extended Stay Hotels in Bloomfield
- Pet-friendly Hotels in Bloomfield
- Casino Hotels in Bloomfield
- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
- Car rentals near Pittsburgh
- Car rentals near University of Pittsburgh Medical Center
- Luxury Car Rentals near University of Pittsburgh Medical Center
- Car rentals near University of Pittsburgh
- Car rentals near Heinz Memorial Chapel
- Car rentals near Phipps Conservatory
- Car rentals near Carnegie Mellon University
- Premium Car Rentals near Carnegie Mellon University
- Car rentals near UPMC Shadyside
- Car rentals near Shadyside
- Hertz Rental Cars in Shadyside
- Enterprise Rental Cars in Shadyside
- SurPrice Car Rentals Rental Cars in Shadyside
- Car rentals near Bloomfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.